CN103030565A - Synthesis process of methylparaben - Google Patents
Synthesis process of methylparaben Download PDFInfo
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- CN103030565A CN103030565A CN 201110303749 CN201110303749A CN103030565A CN 103030565 A CN103030565 A CN 103030565A CN 201110303749 CN201110303749 CN 201110303749 CN 201110303749 A CN201110303749 A CN 201110303749A CN 103030565 A CN103030565 A CN 103030565A
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- microwave
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- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims abstract description 16
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 12
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 12
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 title abstract description 4
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 title abstract description 4
- 229960002216 methylparaben Drugs 0.000 title abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 30
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000002148 esters Chemical class 0.000 claims abstract description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims abstract description 8
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 239000007787 solid Substances 0.000 claims abstract description 5
- 238000001035 drying Methods 0.000 claims abstract description 4
- 238000001914 filtration Methods 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims abstract description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 claims abstract description 4
- 238000005406 washing Methods 0.000 claims abstract description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 238000004080 punching Methods 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 235000019249 food preservative Nutrition 0.000 abstract description 3
- 239000005452 food preservative Substances 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000012295 chemical reaction liquid Substances 0.000 abstract 2
- 238000001704 evaporation Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 abstract 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 abstract 1
- 235000013305 food Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000004278 EU approved seasoning Substances 0.000 description 1
- -1 Tegosept E ester Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004403 ethyl p-hydroxybenzoate Substances 0.000 description 1
- 229940043351 ethyl-p-hydroxybenzoate Drugs 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- 239000011964 heteropoly acid Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 235000019991 rice wine Nutrition 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000013555 soy sauce Nutrition 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a synthesis process of food preservative, and in particular relates to a synthesis process of methylparaben. The synthesis process of methylparaben is simple in operation, short in time consumption and low in pollution. The synthesis process comprises the steps of: adding p-hydroxybenzoic acid and methanol into a round-bottom flask according to the molar ratio of (1: 1.5)-(1: 4.0), and then adding 0.1-0.6g/ g of catalyst sodium hydrogen sulfate into the mixture; putting the round-bottom flask into a microwave oven; preheating to dissolve the raw materials, adjusting the microwave output power to 450W after dissolving and further heating; timing when distillate appears in a water separator; carrying out reaction for 3-18minuest, then pouring out reaction liquid, and leaving the catalyst in a solid state in the round-bottom flask; distilling the reaction liquid, evaporating out excessive methanol, pouring 5% of sodium hydrogen carbonate while hot, and separating out ester from water; and filtering, washing and drying to obtain the finished product.
Description
Technical field:
The present invention relates to a kind of synthesis technique of food preservatives, more particularly, relate to the synthesis technique of Tegosept M.
Background technology:
Tegosept M has another name called methyl p-hydroxybenzoate, and molecular formula is C
8H
8O
3, structural formula is as shown below.
Tegosept M
Nipagin esters is the broad spectrum efficient food sanitas of generally acknowledging in the world, and the states such as the U.S., Europe, Japan, Canada, Korea S, Russia all allow nipagin esters to use in food.Be widely used in the fields such as the seasonings such as soy sauce, vinegar, curing food, bakery, jam product, beverage, yellow rice wine and preserving fruit and vegetable utilizing.Regulation ethyl p-hydroxybenzoate, propylben and soluble metyl hydroxybenzoate, nipagin A sodium, propylben sodium salt can be used as food preservatives among China GB2760.
Nipagin esters is owing to having phenolic hydroxyl structure, so the antibacterium performance is all stronger than phenylformic acid, Sorbic Acid.Its mechanism of action is: the cytolemma of destroy microorganisms makes intracellular protein denaturation, and can suppress the activity of respiratory enzyme system with the electronics transmission enzyme system of microorganism cells.The bacteriostatic activity of nipagin esters mainly is that molecular state works, and its esterification of intramolecular hydroxyl, and no longer ionization is so it all has good fungistatic effect in the scope of pH3～8.
The Tegosept E ester synthesis forms take pure and mild P-hydroxybenzoic acid as the raw material esterification normally take the vitriol oil as catalyzer, and this method has poor product quality, product separation difficulty, waste liquid etching apparatus, the shortcomings such as contaminate environment.In recent years, occurred with solid super-strong acid and the synthetic method of indissoluble heteropoly acid catalysis, but the preparation of this method catalyzer is complicated, long reaction time.
Summary of the invention:
The present invention is exactly for the problems referred to above, and a kind of short, synthesis technique of polluting little Tegosept M simple to operate, consuming time is provided.
In order to realize above-mentioned purpose of the present invention, the present invention adopts following technical scheme, processing step of the present invention is: the adding mol ratio is 1: 1.5～1: 4.0 P-hydroxybenzoic acid and methyl alcohol in round-bottomed flask, then adds catalyst sulfuric acid hydrogen sodium 0.1～0.6g/g; Flask is placed microwave cavity, and flask links to each other with stirring and minute water condensing unit in the external world by three mouthfuls of pipe connectings that place microwave oven top punching place; Preheating makes material dissolution, after having dissolved microwave output power is transferred to 450W and continues heating, begins to clock when beginning distillate to occur in the water trap; Behind reaction 3～18min, inclining reaction solution, and catalyzer is solid and stays in the flask; Reaction solution is distilled, steam excessive methyl alcohol, the sodium bicarbonate aqueous solution of while hot impouring 5%, ester is separated out from water; After filtration, washing and drying obtain thick ester; Thick ester is made with extra care with recrystallization method.
Reaction equation is:
Beneficial effect of the present invention:
1. catalyzer of the present invention is easy to get, stable in properties, and easily separated, reclaim and regeneration;
2. the present invention is little to the corrosion of equipment, does not pollute;
3. the present invention is simple to operate, and is consuming time short;
4. yield of the present invention is 95.52%.
Embodiment:
Processing step of the present invention is: the adding mol ratio is 1: 1.5～1: 4.0 P-hydroxybenzoic acid and methyl alcohol in round-bottomed flask, then adds catalyst sulfuric acid hydrogen sodium 0.1～0.6g/g; Flask is placed microwave cavity, and flask links to each other with stirring and minute water condensing unit in the external world by three mouthfuls of pipe connectings that place microwave oven top punching place; Preheating makes material dissolution, after having dissolved microwave output power is transferred to 450W and continues heating, begins to clock when beginning distillate to occur in the water trap; Behind reaction 3～18min, inclining reaction solution, and catalyzer is solid and stays in the flask; Reaction solution is distilled, steam excessive methyl alcohol, the sodium bicarbonate aqueous solution of while hot impouring 5%, ester is separated out from water; After filtration, washing and drying obtain thick ester; Thick ester is made with extra care with recrystallization method.
Reaction equation is:
As a kind of preferred version, processing step of the present invention is: the mol ratio of P-hydroxybenzoic acid and methyl alcohol is 1: 2.5, and catalyst levels accounts for 3.5% of gross weight, and microwave irradiation time is 18min.
End product structure of the present invention has obtained the affirmation of infrared spectrum.
Claims (2)
1. the synthesis technique of Tegosept M, it is characterized in that, the present invention adopts following technical scheme, and processing step of the present invention is: the adding mol ratio is 1: 1.5～1: 4.0 P-hydroxybenzoic acid and methyl alcohol in round-bottomed flask, then adds catalyst sulfuric acid hydrogen sodium 0.1～0.6g/g; Flask is placed microwave cavity, and flask links to each other with stirring and minute water condensing unit in the external world by three mouthfuls of pipe connectings that place microwave oven top punching place; Preheating makes material dissolution, after having dissolved microwave output power is transferred to 450W and continues heating, begins to clock when beginning distillate to occur in the water trap; Behind reaction 3～18min, inclining reaction solution, and catalyzer is solid and stays in the flask; Reaction solution is distilled, steam excessive methyl alcohol, the sodium bicarbonate aqueous solution of while hot impouring 5%, ester is separated out from water; After filtration, washing and drying obtain thick ester; Thick ester is made with extra care with recrystallization method
Reaction equation is:
2. the synthesis technique of Tegosept M according to claim 1 is characterized in that, processing step of the present invention is: the mol ratio of P-hydroxybenzoic acid and methyl alcohol is 1: 2.5, and catalyst levels accounts for 3.5% of gross weight, and microwave irradiation time is 18min.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201110303749 CN103030565A (en) | 2011-10-10 | 2011-10-10 | Synthesis process of methylparaben |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201110303749 CN103030565A (en) | 2011-10-10 | 2011-10-10 | Synthesis process of methylparaben |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103030565A true CN103030565A (en) | 2013-04-10 |
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ID=48018015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 201110303749 Pending CN103030565A (en) | 2011-10-10 | 2011-10-10 | Synthesis process of methylparaben |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103030565A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106349069A (en) * | 2016-08-30 | 2017-01-25 | 芜湖华海生物工程有限公司 | Preparation method of methyl p hydroxybenzoate |
-
2011
- 2011-10-10 CN CN 201110303749 patent/CN103030565A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106349069A (en) * | 2016-08-30 | 2017-01-25 | 芜湖华海生物工程有限公司 | Preparation method of methyl p hydroxybenzoate |
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|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20130410 |